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Vaer A5 Design Navy Automatic Watch ($499)

The durable, American-assembled comes with two bands of your choosing. Take advantage of the waterproof silicone strap, 10ATM water-resistance rating, and scratch-resistant sapphire crystal face at play time, then switch to the Horween leather to dress things up.

Beltology Litmus Belt ($95)

Thanks to Beltology’s signature flex, the Litmus gives you room for waistline expansion. This woven Italian leather and nickel belt looks so nice, no one will know you’re insanely comfortable.

Hestra John Gloves ($150)

With its smooth Hairsheep leather and rib-knitted wool cuffs, this glove looks classy on the outside but is all function on the inside. Light PrimaLoft insulation with brushed polyester lining keep your hands toasty, while touchscreen pads on the index finger and thumb let you use your smartphone with them on.

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Tracksmith New England Overshirt ($198)

Tracksmith built the perfect overshirt for runners. The recycled wool, cotton, and nylon blend leaves plenty of stretch for movement and the relaxed comfort you want for a busy day ahead. And thanks to the odor-resisting properties of wool and the durability of nylon, you can put more than a few miles in it. The end result? A classically styled overshirt meant for getting work done—whether it be on the roads or in the office.

Randolph Hamilton Sunglasses ($269 and up)

The hexagonal frame of these unisex 22-karat gold shades harkens back to the 1920s. The attention to detail is also old school—Randolph glasses are designed and handcrafted in the USA and guaranteed for life.

The North Face Men’s Berkeley Cord Overshirt ($89)

The relaxed fit makes this comfy shirt easy to throw over a sweater. A smaller slot in the chest pocket is perfect for separating sundries.

Topo Designs Men’s Dirt Shirt ($98)

Don’t let the name fool you—this stretchy button-up is sharp enough for the whiskey bar. It’s 98 percent organic cotton and made using a water-friendly dyeing process.

Mott and Bow the Twill Chino Charles Pants ($125)

After spending 2020 in sweatpants, elevate your look with the Charles, a slim-fit medium-weight pair of khakis. With three percent elastane, you’ll still be comfy.

OluKai Kalia Puki Boots ($165)

Functional enough for exploration but classy enough for cocktails, the Kalia Puki sports an outsole designed for grip in wet conditions and a comfortable gel-insert footbed lined with microfiber.

Fjällräven Expedition Long Down Parka ($600)

This knee-length parka features drawcord adjustments throughout, a protective flap over the zipper, elastic cuffs, and an extra-high neckline to fortify against the cold. If that weren’t enough, it also boasts ethically sourced down, a recycled nylon shell, and PFC-free DWR.